The article considers the main stages of settling and economic development of the Kulikovo field area starting from the 12th century on the case of a site typical in landscape and geomorphological terms. A retrospective analysis of the material characterized lands’ orientation and territorial organization at each stage was carried out. Data are given on the degree of anthropogenic transformation of the original landscape structure at various stages of settling and economic development of the territory. The first, Old Russian period (12th–14th centuries) and the next late medieval period (16th–17th centuries) are characterized by a weak degree of anthropogenic transformation. Agriculture used no more than 30% of the original forest area. Anthropogenic complexes consisted of long-term arable land and the settlements’ territory. Forest edges and abandoned arable lands were used for pastures and hayfields. During the new stage (17th–the end of the 19th centuries), the expansion of arable land is carried out at the expense of deforestation, as in the previous stage. The reason is the use of extensive agronomic technologies. In the second half of the 18th century, the degree of anthropogenic transformation has become strong. More than 50% of the forest area has been cut down. Agricultural plots (perennial arable lands, hay, and pasture lands) appeared on the site of the cut down forest. By the end of the 19th century, forests occupy less than 10% of the territory and are represented by secondary or restored forests. The degree of anthropogenic transformation becomes very strong. Agricultural land, together with settlements, covers more than 90% of the territory. These are arable lands, hayfields, and pastures that have existed at certain geomorphological levels for centuries. Thus, by the beginning of the 20th century, there was a radical restructuring of the original natural landscape structure. On the watershed of the Don and Mokraya Tabola rivers, an agricultural landscape of the modern type was formed.